title: Transformation of anionically activated trifluoromethyl groups to heterocycles under mild aqueous conditions.
abstract: The (hetero)aromatic trifluoromethyl group is present in many biologically active molecules and is generally considered to be chemically stable. In this paper, a convenient one-step synthesis of C-C linked aryl-heterocycles or heteroaryl-heterocycles in good to excellent yields via the reaction of anionically activated trifluoromethyl groups with amino nucleophiles containing a second NH, OH, or SH nucleophile in 1 N sodium hydroxide is reported. The method has high functional group tolerability and is potentially useful in parallel synthesis.
authors.affiliation: Research & Development, Bristol-Myers Squibb Company, Princeton, New Jersey 08543, United States. Jennifer.qiao@bms.com
authors.forename: Jennifer X
authors.initials: JX
authors.lastname: Qiao
authors.forename: Tammy C
authors.initials: TC
authors.lastname: Wang
authors.forename: Carol
authors.initials: C
authors.lastname: Hu
authors.forename: Jianqing
authors.initials: J
authors.lastname: Li
authors.forename: Ruth R
authors.initials: RR
authors.lastname: Wexler
authors.forename: Patrick Y S
authors.initials: PY
authors.lastname: Lam
mesh_terms: D000838:Anions / Q000737:chemistry; D017611:Fluorine Compounds / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000838:Anions; D017611:Fluorine Compounds; D006571:Heterocyclic Compounds